Sodium hydride → HCID 21912078, Verbindung

HRID 968028

Reaktionsgleichung

Reaktionsgleichung von HRID 968028
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]#[N:11].[H-].[Na+].[CH3:15][C:16]1[N:21]=[C:20](Cl)[C:19]([CH3:23])=[C:18]([Cl:24])[N:17]=1>C1COCC1>[Cl:24][C:18]1[N:17]=[C:16]([CH3:15])[N:21]=[C:20]([CH:9]([C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:12])[C:10]#[N:11])[C:19]=1[CH3:23]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2370134,6-Dichloro-2,5-dimethylpyrimidineHCID 5206982,4,6-Trimethylphenylacetonitrile

Produkt 1

HCID 21912078HCID 21912078, VerbindungAusbeute 106,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of mesitylacetonitrile (0.900 g, 5.65 mmol) in 8 ml dry THF was added sodium hydride (60% in oil, 0.250 g, 6.21 mmol) and the mixture was stirred at room temperature for 40 minutes. 2,5-Dimethyl-4,6-dichloropyrimidine (1.000 g, 5.65 mmol) was added and the resulting mixture was heated at reflux for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 1.800 g of a yellow oil. The oil residue was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 0.986 g (58.3%) of the title compound as a white solid, mp 100-102° C. 1H NMR (CDCl3) δ 6.86 (s, 2H), 5.60 (s, 1H), 2.69 (s, 3H), 2.25 (s, 3H), 2.18 (s, 6H), 1.92 (s, 3H) ppm.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e8f66468e9d436d8ca19eb479cc6b02
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956047B1

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